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Preparation of 6-demethoxythebaine from neopine and its Diels-Alder reaction with ethyl acrylate (Chemistry of opium alkaloids, Part XV)

✍ Scribed by P. R. Crabbendam; L. Maat; H. C. Beyerman

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
171 KB
Volume
100
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

6α‐O‐Methanesulfonylneopine (3b) was converted into 6‐demethoxythebaine (4b) with the aid of potassium tert‐butoxide. Diels‐Alder reaction of 6‐demethoxythebaine with ethyl acrylate yielded mainly 4,5‐epoxy‐6,14‐endo‐etheno‐7α‐ethoxycarbonyl‐3‐methoxy‐17‐methylmorphinan (5b), an intermediate for the synthesis of potential analgesics.

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